Aqua­(cyanido-κC){6,6′-dimeth­oxy-2,2′-[o-phenyl­enebis(nitrilo­methanylyl­idene)]diphenolato-κ4O1,N,N′,O1′}cobalt(III) acetonitrile monosolvate

Lin, Y.; Li, G.-M.; Chen, P.; Yan, P.-F.; Hou, G.-F.

doi:10.1107/S1600536811029461

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1162

doi:10.1107/S1600536811029461

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Aqua(cyanido-κC){6,6′-dimethoxy-2,2′-[o-phenylenebis(nitrilomethanylylidene)]diphenolato-κ⁴O¹,N,N′,O^1′}cobalt(III) acetonitrile monosolvate

Yang Lin,^a Guang-Ming Li,^a ^* Peng Chen,^a Peng-Fei Yan ^a and Guang-Feng Hou ^a

^aKey Laboratory of Functional Inorganic Materials Chemistry (MOE), School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli_2000@163.com

(Received 13 July 2011; accepted 21 July 2011; online 30 July 2011)

In the title complex, [Co(C₂₂H₁₈N₂O₄)(CN)(H₂O)]·CH₃CN, the Co^III ion is six-coordinated in a distorted octahedral environment defined by two N atoms and two O atoms from a salen ligand in the equatorial plane and one O atom from a water molecule and one C atom from a cyanide group at the axial positions. O—H⋯O hydrogen bonds connect adjacent complex molecules into dimers. C—H⋯N hydrogen bonds and π–π interactions between the benzene rings [centroid–centroid distances = 3.700 (2) and 3.845 (2) Å] are also present.

Related literature

For the synthesis of the ligand, see: Costes et al. (2000 ). For related transition-metal complexes, see: Przychodzeń et al. (2005 ). For bond-valence calculations, see: Spek (2009 ).

Experimental

Crystal data

[Co(C₂₂H₁₈N₂O₄)(CN)(H₂O)]·C₂H₃N
M_r = 518.40
Monoclinic, P 2₁ /c
a = 10.829 (2) Å
b = 13.209 (3) Å
c = 18.906 (6) Å
β = 118.30 (2)°
V = 2381.1 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 293 K
0.34 × 0.31 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.780, T_max = 0.811
22543 measured reflections
5426 independent reflections
4439 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.08
5426 reflections
319 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—C23	1.869 (2)
Co1—N1	1.8944 (15)
Co1—N2	1.8972 (16)
Co1—O1	1.8948 (13)
Co1—O2	1.8998 (14)
Co1—O5	2.0194 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O3ⁱ	0.85	2.33	2.922 (2)	127
O5—H51⋯O1ⁱ	0.85	2.00	2.799 (2)	156
O5—H52⋯O2ⁱ	0.85	2.24	2.813 (2)	124
O5—H52⋯O4ⁱ	0.85	2.10	2.902 (2)	158
C10—H10⋯N4ⁱⁱ	0.93	2.61	3.433 (3)	148
C15—H15⋯N3	0.93	2.56	3.440 (3)	159
Symmetry codes: (i) -x+2, -y, -z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029461/hy2451sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029461/hy2451Isup2.hkl

checkCIF report

Comment top

Transition metal complexes with spectroscopic and magnetic properties are currently of considerable interest. As a continuing work for the studies of salen ligands (Costes et al., 2000) and transition metal complexes (Przychodzeń et al., 2005), we present here the synthesis and crystal structure of the title compound.

The bond valence calculation (Spek, 2009) indicated that the Co atom is in a 3+ state, which can be produced by Li(TCNQ) oxidating Co(II) atom [TCNQ = 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis(propanedinitrile)]. Meanwhile, TCNQ decomposed to produce cyanide group. In the title complex, the Co^III ion is six-coordinated in a distorted octahedral environment defined by two imino N atoms and two phenolate O atoms from the salen type ligand, one O atom from a water molecule and one C atom from a cyanide group (Fig. 1, Table 1). O—H···O hydrogen bonds connect two adjacent complex molecules into a dimer (Fig. 2, Table 2). C—H···N hydrogen bonds and π–π interactions between the benzene rings [centroid–centroid distance = 3.700 (2) and 3.845 (2) Å] are present.

Related literature top

For the synthesis of the ligand, see: Costes et al. (2000). For related transition-metal complexes, see: Przychodzeń et al. (2005). For bond-valence calculations, see: Spek (2009).

Experimental top

A solution of CoL (0.078 g, 0.1 mmol) [L = N,N'-bis(3-methoxy-2-oxidobenzylidene) -1,2-diaminobenzene] (Costes et al., 2000) in CH₃CN (25 ml) was added dropwise to a solution of LiTCNQ (0.044 g, 0.2 mmol) in H₂O (20 ml). The reaction was carried out under nitrogen atmosphere, using standard Schlenk techniques and degassed solvents. Reddish brown single crystals suitable for X-ray analysis were obtained in five days. Analysis, calculated for C₂₅H₂₃CoN₄O₅: C 57.81, H 4.66, N 10.79; found: C 57.76, H 4.74, N 10.83%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the hydrogen-bonded dimer, showing hydrogen bonds (green dashed lines) and π–π interactions (blue dashed lines).

Aqua(cyanido-κC){6,6'-dimethoxy-2,2'-[o- phenylenebis(nitrilomethanylylidene)]diphenolato- κ⁴O¹,N,N',O^1'}cobalt(III) acetonitrile monosolvate top

Crystal data top

[Co(C₂₂H₁₈N₂O₄)(CN)(H₂O)]·C₂H₃N	F(000) = 1072
M_r = 518.40	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17687 reflections
a = 10.829 (2) Å	θ = 3.1–27.5°
b = 13.209 (3) Å	µ = 0.77 mm⁻¹
c = 18.906 (6) Å	T = 293 K
β = 118.30 (2)°	Block, brown
V = 2381.1 (10) Å³	0.34 × 0.31 × 0.29 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5426 independent reflections
Radiation source: fine-focus sealed tube	4439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→14
T_min = 0.780, T_max = 0.811	k = −17→17
22543 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.046P)² + 0.9325P] where P = (F_o² + 2F_c²)/3
5426 reflections	(Δ/σ)_max = 0.001
319 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Co(C₂₂H₁₈N₂O₄)(CN)(H₂O)]·C₂H₃N	V = 2381.1 (10) Å³
M_r = 518.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.829 (2) Å	µ = 0.77 mm⁻¹
b = 13.209 (3) Å	T = 293 K
c = 18.906 (6) Å	0.34 × 0.31 × 0.29 mm
β = 118.30 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5426 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4439 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.811	R_int = 0.034
22543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.08	Δρ_max = 0.36 e Å⁻³
5426 reflections	Δρ_min = −0.35 e Å⁻³
319 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5547 (3)	0.1426 (2)	−0.19502 (14)	0.0647 (8)
H1A	0.5301	0.0812	−0.2259	0.097*
H1B	0.5808	0.1932	−0.2219	0.097*
H1C	0.4757	0.1661	−0.1896	0.097*
C2	0.7165 (2)	0.20216 (16)	−0.06373 (12)	0.0371 (4)
C3	0.6721 (2)	0.30104 (17)	−0.08039 (14)	0.0469 (5)
H3	0.6029	0.3184	−0.1317	0.056*
C4	0.7297 (3)	0.37577 (17)	−0.02117 (15)	0.0504 (6)
H4	0.6997	0.4425	−0.0334	0.060*
C5	0.8296 (2)	0.35112 (16)	0.05426 (14)	0.0441 (5)
H5	0.8671	0.4012	0.0934	0.053*
C6	0.8773 (2)	0.24945 (14)	0.07391 (12)	0.0341 (4)
C7	0.8218 (2)	0.17321 (14)	0.01489 (11)	0.0312 (4)
C8	0.9842 (2)	0.22983 (15)	0.15339 (12)	0.0333 (4)
H8	1.0159	0.2846	0.1885	0.040*
C9	1.1540 (2)	0.13197 (15)	0.26124 (11)	0.0318 (4)
C10	1.2143 (2)	0.21081 (16)	0.31618 (12)	0.0405 (5)
H10	1.1825	0.2769	0.3018	0.049*
C11	1.3210 (2)	0.18993 (18)	0.39164 (13)	0.0469 (5)
H11	1.3610	0.2422	0.4286	0.056*
C12	1.3696 (2)	0.09200 (19)	0.41328 (13)	0.0466 (5)
H12	1.4418	0.0790	0.4647	0.056*
C13	1.3121 (2)	0.01354 (17)	0.35951 (12)	0.0401 (5)
H13	1.3456	−0.0521	0.3743	0.048*
C14	1.2030 (2)	0.03317 (14)	0.28252 (11)	0.0316 (4)
C15	1.1581 (2)	−0.13640 (15)	0.23320 (11)	0.0323 (4)
H15	1.2264	−0.1561	0.2841	0.039*
C16	0.9948 (2)	−0.19407 (14)	0.09435 (11)	0.0300 (4)
C17	1.0922 (2)	−0.21447 (14)	0.17560 (11)	0.0324 (4)
C18	1.1305 (2)	−0.31644 (15)	0.20116 (13)	0.0397 (5)
H18	1.1953	−0.3296	0.2544	0.048*
C19	1.0737 (3)	−0.39453 (16)	0.14897 (14)	0.0455 (5)
H19	1.0989	−0.4608	0.1666	0.055*
C20	0.9769 (2)	−0.37543 (15)	0.06817 (13)	0.0419 (5)
H20	0.9385	−0.4292	0.0326	0.050*
C21	0.9386 (2)	−0.27817 (15)	0.04140 (12)	0.0345 (4)
C22	0.7825 (3)	−0.32967 (19)	−0.09336 (14)	0.0562 (7)
H22A	0.7288	−0.3007	−0.1458	0.084*
H22B	0.7218	−0.3684	−0.0797	0.084*
H22C	0.8537	−0.3731	−0.0932	0.084*
C23	0.8551 (2)	−0.00903 (15)	0.15346 (12)	0.0348 (4)
Co1	0.99408 (3)	0.018833 (18)	0.124299 (14)	0.02757 (9)
N1	1.04207 (17)	0.14260 (11)	0.18179 (9)	0.0293 (3)
N2	1.13171 (17)	−0.03998 (12)	0.22136 (9)	0.0296 (3)
N4	0.7711 (2)	−0.02985 (16)	0.17105 (14)	0.0538 (5)
O1	0.95350 (15)	−0.10306 (10)	0.06457 (7)	0.0332 (3)
O2	0.86109 (14)	0.07822 (10)	0.02591 (8)	0.0343 (3)
O3	0.84670 (17)	−0.25085 (11)	−0.03599 (8)	0.0434 (4)
O4	0.66969 (16)	0.12382 (12)	−0.11736 (9)	0.0465 (4)
O5	1.14913 (14)	0.04801 (10)	0.09656 (8)	0.0339 (3)
H51	1.1136	0.0809	0.0527	0.051*
H52	1.1992	0.0032	0.0901	0.051*
N3	1.4525 (3)	−0.2365 (3)	0.39165 (18)	0.1011 (11)
C24	1.4969 (3)	−0.3138 (3)	0.41113 (18)	0.0685 (8)
C25	1.5580 (4)	−0.4129 (3)	0.4384 (3)	0.1254 (18)
H25A	1.6559	−0.4058	0.4759	0.188*
H25B	1.5474	−0.4524	0.3933	0.188*
H25C	1.5113	−0.4461	0.4643	0.188*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0577 (16)	0.0727 (19)	0.0373 (12)	0.0148 (13)	0.0009 (11)	0.0020 (12)
C2	0.0379 (11)	0.0340 (10)	0.0368 (10)	0.0067 (8)	0.0156 (9)	0.0031 (9)
C3	0.0467 (13)	0.0404 (12)	0.0450 (12)	0.0148 (10)	0.0148 (10)	0.0137 (10)
C4	0.0585 (14)	0.0275 (10)	0.0612 (14)	0.0144 (10)	0.0251 (12)	0.0115 (11)
C5	0.0518 (13)	0.0264 (10)	0.0522 (13)	0.0078 (9)	0.0231 (11)	0.0017 (10)
C6	0.0374 (10)	0.0254 (9)	0.0409 (10)	0.0058 (8)	0.0197 (9)	0.0021 (8)
C7	0.0333 (10)	0.0283 (9)	0.0353 (10)	0.0063 (7)	0.0191 (8)	0.0039 (8)
C8	0.0424 (11)	0.0246 (9)	0.0371 (10)	0.0006 (8)	0.0221 (9)	−0.0045 (8)
C9	0.0343 (10)	0.0296 (10)	0.0297 (9)	−0.0027 (8)	0.0137 (8)	−0.0032 (8)
C10	0.0450 (12)	0.0314 (10)	0.0392 (11)	−0.0020 (9)	0.0152 (9)	−0.0068 (9)
C11	0.0490 (13)	0.0429 (13)	0.0393 (11)	−0.0096 (10)	0.0132 (10)	−0.0138 (10)
C12	0.0419 (12)	0.0524 (14)	0.0317 (10)	−0.0052 (10)	0.0063 (9)	−0.0039 (10)
C13	0.0396 (11)	0.0374 (11)	0.0342 (10)	−0.0005 (9)	0.0101 (9)	0.0020 (9)
C14	0.0340 (10)	0.0298 (10)	0.0297 (9)	−0.0024 (7)	0.0142 (8)	−0.0015 (8)
C15	0.0366 (10)	0.0300 (10)	0.0286 (9)	0.0033 (8)	0.0142 (8)	0.0044 (8)
C16	0.0376 (10)	0.0213 (8)	0.0336 (9)	0.0009 (7)	0.0190 (8)	0.0002 (8)
C17	0.0391 (11)	0.0245 (9)	0.0338 (9)	0.0024 (8)	0.0176 (8)	0.0027 (8)
C18	0.0493 (12)	0.0290 (10)	0.0386 (11)	0.0070 (9)	0.0192 (10)	0.0072 (9)
C19	0.0622 (15)	0.0221 (10)	0.0511 (13)	0.0055 (9)	0.0261 (11)	0.0056 (9)
C20	0.0582 (14)	0.0241 (10)	0.0439 (11)	−0.0022 (9)	0.0246 (10)	−0.0056 (9)
C21	0.0416 (11)	0.0273 (10)	0.0340 (10)	−0.0020 (8)	0.0175 (9)	−0.0022 (8)
C22	0.0664 (16)	0.0424 (13)	0.0420 (12)	−0.0086 (12)	0.0110 (12)	−0.0140 (11)
C23	0.0384 (11)	0.0269 (9)	0.0352 (10)	−0.0009 (8)	0.0143 (9)	−0.0044 (8)
Co1	0.03420 (15)	0.02039 (13)	0.02460 (13)	0.00213 (10)	0.01105 (10)	−0.00039 (10)
N1	0.0368 (9)	0.0240 (8)	0.0277 (7)	0.0003 (6)	0.0158 (7)	−0.0023 (6)
N2	0.0343 (8)	0.0262 (8)	0.0264 (7)	0.0000 (6)	0.0130 (6)	−0.0009 (6)
N4	0.0546 (12)	0.0493 (12)	0.0678 (14)	−0.0096 (10)	0.0373 (11)	−0.0099 (10)
O1	0.0463 (8)	0.0212 (6)	0.0261 (6)	0.0023 (5)	0.0123 (6)	−0.0006 (5)
O2	0.0420 (8)	0.0260 (7)	0.0286 (6)	0.0069 (6)	0.0116 (6)	0.0004 (5)
O3	0.0547 (9)	0.0283 (7)	0.0341 (7)	−0.0033 (6)	0.0104 (7)	−0.0058 (6)
O4	0.0471 (9)	0.0422 (9)	0.0346 (8)	0.0103 (7)	0.0067 (7)	0.0018 (7)
O5	0.0400 (7)	0.0303 (7)	0.0324 (7)	0.0050 (6)	0.0180 (6)	0.0024 (6)
N3	0.087 (2)	0.088 (2)	0.088 (2)	0.0309 (18)	0.0079 (17)	0.0136 (18)
C24	0.0522 (16)	0.073 (2)	0.0594 (16)	0.0092 (14)	0.0092 (13)	−0.0069 (15)
C25	0.083 (3)	0.059 (2)	0.185 (5)	0.0098 (19)	0.023 (3)	−0.001 (3)

Geometric parameters (Å, º) top

C1—O4	1.426 (3)	C15—C17	1.422 (3)
C1—H1A	0.9600	C15—H15	0.9300
C1—H1B	0.9600	C16—O1	1.313 (2)
C1—H1C	0.9600	C16—C17	1.417 (3)
C2—O4	1.367 (3)	C16—C21	1.424 (3)
C2—C3	1.376 (3)	C17—C18	1.425 (3)
C2—C7	1.431 (3)	C18—C19	1.357 (3)
C3—C4	1.398 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.406 (3)
C4—C5	1.359 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.371 (3)
C5—C6	1.424 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—O3	1.372 (2)
C6—C7	1.409 (3)	C22—O3	1.424 (3)
C6—C8	1.420 (3)	C22—H22A	0.9600
C7—O2	1.309 (2)	C22—H22B	0.9600
C8—N1	1.300 (2)	C22—H22C	0.9600
C8—H8	0.9300	C23—N4	1.140 (3)
C9—C14	1.394 (3)	Co1—C23	1.869 (2)
C9—C10	1.395 (3)	Co1—N1	1.8944 (15)
C9—N1	1.421 (2)	Co1—N2	1.8972 (16)
C10—C11	1.372 (3)	Co1—O1	1.8948 (13)
C10—H10	0.9300	Co1—O2	1.8998 (14)
C11—C12	1.383 (3)	Co1—O5	2.0194 (14)
C11—H11	0.9300	O5—H51	0.8500
C12—C13	1.377 (3)	O5—H52	0.8500
C12—H12	0.9300	N3—C24	1.114 (4)
C13—C14	1.397 (3)	C24—C25	1.447 (5)
C13—H13	0.9300	C25—H25A	0.9600
C14—N2	1.421 (2)	C25—H25B	0.9600
C15—N2	1.301 (2)	C25—H25C	0.9600

O4—C1—H1A	109.5	C19—C18—C17	120.90 (19)
O4—C1—H1B	109.5	C19—C18—H18	119.6
H1A—C1—H1B	109.5	C17—C18—H18	119.6
O4—C1—H1C	109.5	C18—C19—C20	120.06 (19)
H1A—C1—H1C	109.5	C18—C19—H19	120.0
H1B—C1—H1C	109.5	C20—C19—H19	120.0
O4—C2—C3	125.62 (19)	C21—C20—C19	120.55 (19)
O4—C2—C7	113.63 (17)	C21—C20—H20	119.7
C3—C2—C7	120.7 (2)	C19—C20—H20	119.7
C2—C3—C4	120.8 (2)	C20—C21—O3	125.44 (18)
C2—C3—H3	119.6	C20—C21—C16	121.19 (19)
C4—C3—H3	119.6	O3—C21—C16	113.37 (17)
C5—C4—C3	120.1 (2)	O3—C22—H22A	109.5
C5—C4—H4	119.9	O3—C22—H22B	109.5
C3—C4—H4	119.9	H22A—C22—H22B	109.5
C4—C5—C6	120.6 (2)	O3—C22—H22C	109.5
C4—C5—H5	119.7	H22A—C22—H22C	109.5
C6—C5—H5	119.7	H22B—C22—H22C	109.5
C7—C6—C8	122.36 (17)	N4—C23—Co1	177.41 (19)
C7—C6—C5	120.13 (19)	C23—Co1—N1	92.35 (8)
C8—C6—C5	117.48 (19)	C23—Co1—O1	90.96 (7)
O2—C7—C6	125.07 (17)	N1—Co1—O1	176.68 (7)
O2—C7—C2	117.38 (17)	C23—Co1—N2	90.42 (8)
C6—C7—C2	117.53 (17)	N1—Co1—N2	85.55 (7)
N1—C8—C6	126.20 (18)	O1—Co1—N2	94.73 (6)
N1—C8—H8	116.9	C23—Co1—O2	91.57 (8)
C6—C8—H8	116.9	N1—Co1—O2	94.58 (6)
C14—C9—C10	120.28 (18)	O1—Co1—O2	85.03 (6)
C14—C9—N1	114.50 (16)	N2—Co1—O2	178.00 (7)
C10—C9—N1	125.23 (18)	C23—Co1—O5	178.11 (7)
C11—C10—C9	119.3 (2)	N1—Co1—O5	87.05 (6)
C11—C10—H10	120.3	O1—Co1—O5	89.65 (6)
C9—C10—H10	120.3	N2—Co1—O5	87.75 (6)
C10—C11—C12	120.7 (2)	O2—Co1—O5	90.26 (6)
C10—C11—H11	119.7	C8—N1—C9	121.80 (16)
C12—C11—H11	119.7	C8—N1—Co1	125.49 (14)
C13—C12—C11	120.7 (2)	C9—N1—Co1	112.69 (12)
C13—C12—H12	119.7	C15—N2—C14	122.36 (16)
C11—C12—H12	119.7	C15—N2—Co1	125.09 (13)
C12—C13—C14	119.5 (2)	C14—N2—Co1	112.53 (12)
C12—C13—H13	120.2	C16—O1—Co1	125.94 (12)
C14—C13—H13	120.2	C7—O2—Co1	126.13 (12)
C9—C14—C13	119.50 (18)	C21—O3—C22	117.74 (17)
C9—C14—N2	114.59 (16)	C2—O4—C1	117.87 (19)
C13—C14—N2	125.90 (18)	Co1—O5—H51	107.7
N2—C15—C17	126.06 (18)	Co1—O5—H52	124.8
N2—C15—H15	117.0	H51—O5—H52	103.9
C17—C15—H15	117.0	N3—C24—C25	178.4 (4)
O1—C16—C17	124.47 (17)	C24—C25—H25A	109.5
O1—C16—C21	117.89 (17)	C24—C25—H25B	109.5
C17—C16—C21	117.64 (17)	H25A—C25—H25B	109.5
C16—C17—C15	122.53 (17)	C24—C25—H25C	109.5
C16—C17—C18	119.65 (18)	H25A—C25—H25C	109.5
C15—C17—C18	117.79 (18)	H25B—C25—H25C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O3ⁱ	0.85	2.33	2.922 (2)	127
O5—H51···O1ⁱ	0.85	2.00	2.799 (2)	156
O5—H52···O2ⁱ	0.85	2.24	2.813 (2)	124
O5—H52···O4ⁱ	0.85	2.10	2.902 (2)	158
C10—H10···N4ⁱⁱ	0.93	2.61	3.433 (3)	148
C15—H15···N3	0.93	2.56	3.440 (3)	159

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₂₂H₁₈N₂O₄)(CN)(H₂O)]·C₂H₃N
M_r	518.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.829 (2), 13.209 (3), 18.906 (6)
β (°)	118.30 (2)
V (Å³)	2381.1 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.34 × 0.31 × 0.29

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.780, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	22543, 5426, 4439
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.08
No. of reflections	5426
No. of parameters	319
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—C23	1.869 (2)	Co1—O1	1.8948 (13)
Co1—N1	1.8944 (15)	Co1—O2	1.8998 (14)
Co1—N2	1.8972 (16)	Co1—O5	2.0194 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O3ⁱ	0.85	2.33	2.922 (2)	127
O5—H51···O1ⁱ	0.85	2.00	2.799 (2)	156
O5—H52···O2ⁱ	0.85	2.24	2.813 (2)	124
O5—H52···O4ⁱ	0.85	2.10	2.902 (2)	158
C10—H10···N4ⁱⁱ	0.93	2.61	3.433 (3)	148
C15—H15···N3	0.93	2.56	3.440 (3)	159

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+2, y+1/2, −z+1/2.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant Nos. 20872030 and 20972043), Heilongjiang Province (grant Nos. 2009RFXXG201, GC09A402 and 2010td03) and Heilongjiang University.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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